Phenacyl bromide → HCID 22179649, compound

HRID 1796662Notes

Reaction equation

HRID 1796662 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][N:6]2[CH:9]=[C:10]([C:13](=[S:15])[NH2:14])[C:11]([CH3:12])=[C:5]2[C:4]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)#[N:2].Br[CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=O>CC(C)=O>[CH3:12][C:11]1[C:10]([C:13]2[S:15][CH:31]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:14]=2)=[CH:9][N:6]2[C:5]=1[C:4]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=1)=[C:3]([C:1]#[N:2])[CH:8]=[N:7]2

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 21025063HCID 21025063, compound

Product 1

HCID 22179649HCID 22179649, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 423A (15 mg, 0.037 mmol) and 2-bromoacetophenone (7.3 mg, 0.037 mmol) in acetone (3 ml) was heated at 70° C. for 1 h. Cooled to rt, hexanes (1 ml) was added, then the resulting mixture was cooled to −50° C., filtered, the solid was washed with hexanes to give the hydrobromide salt of 423 (14.9 mg, 69%) as a yellow powder. It has a retention time of 8.16 min (standard LC1 method, 8 min run). LCMS Found: (M+H)+=500.3

Workup

  1. temperatureCooled to rt
  2. temperaturethe resulting mixture was cooled to −50° C.
  3. filtrationfiltered
  4. washthe solid was washed with hexanes

Sources & evidence

ORD record
ord-e6b52b7f2977406d90589082eecf0955
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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